


First Time

by brokencasbutt67



Series: Supernatural Kink Bingo 2019 [6]
Category: Supernatural
Genre: Anniversary, Engagement, F/M, Fluff, Loss of Virginity, Reader-Insert, Sex in/on the Impala (Supernatural), Smut
Language: English
Status: Completed
Published: 2019-01-13
Updated: 2019-01-13
Packaged: 2019-10-09 15:30:23
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,142
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17409476
Author URL: https://archiveofourown.org/users/brokencasbutt67/pseuds/brokencasbutt67





	First Time

Usually you hated being cramped into the impala for so long. Between the numb ass and lack of leg room, generally you tended to avoid it. Though tonight is different. It’s date night for you and Sam. After finally starting the relationship, that many people thought you were already in, you made an agreement that one night per month would be taken from hunting. No new cases, no travelling motel to motel. Just you, Sam and a date. Usually, it consisted of take out and a movie, and that was one of the most enjoyable types of date. Laid in your underwear, with some shitty movie on the television, you were truly able to relax. But tonight, Sam had told you that the date would be a little different. Handing you and Charlie a credit card, Dean had sent you on your way to buy a new dress that wouldn’t be used for fed cases. You had asked why Sam hadn’t given you it, but Dean just shrugged in response.  
“Prepping for tonight. It’s the big one year after all” Dean shrugged before going on his way. Your eyes widened as you calculated the dates and realised that it had in fact been one year since you and Sam had gotten together, to the approval of all of your friends and family.

 

The mall was packed. So many teenagers filled it, being on summer break. You hated it, you just wanted to be in the bunker, but you’d managed to snatch Sam’s Stanford hoodie before you left, and it calmed the pit of anxiety that was building in your stomach. The first store you came to only had a few dresses left, and none of them looked or felt right. It took three more stores before you finally found the perfect one. Walking out of the fitting room, Charlie’s eyes bulged out of her head.  
“Please turn lesbian” She begged. You blushed and smiled, looking down.  
“Is it…okay?” You asked.  
“More than” She responded. Looking at the price tag, you became disheartened when you saw just how high the price was, it was well out of your price range.  
“Hey” Charlie smirked.  
“You’re not paying for it. Caroline Smith is” She smirked.  
“Good point” You chuckled.  
“But still…” You trailed off.  
“No buts. You look stunning. Get it” Charlie said, though it didn’t take much encouragement to get you to buy the dress. After making the extravagant purchase, you and Charlie both went to dinner. Not knowing what you were having on this date, you decided on Subway and shared a Chicken Tikka melt, though the person making the sandwich didn’t look too pleased about the differences. You loved to have corn, onion, cucumber, mayonnaise and cheese, while Charlie liked the spicier options, so her side had onions, jalapeños and so much more.

 

Sitting on a bench in the sun, you were eating your sandwiches.  
“Shit, what do I get Sam for our anniversary?” You exclaimed.  
“Sex” Charlie shrugged around a mouthful of food.  
“He wants to wait, wants it to be special…” You trailed off, not wanting to tell Charlie the slightly embarrassing reason that you and Sam hadn’t taken that final step, even though you’d done just about everything else.  
“Riiiiight…” Charlie trailed off.  
“I have him a fancy watch hidden that was for his birthday, but then I took him to that…thing…” You trailed off, attempting to remember what boring event you went to, and though Sam knew you weren’t interested in it, it made him happy that you were putting effort into paying an interest in his life and interests.

“Give him that and, I’m guessing here, your first time?” Charlie said, slightly quieter towards the end. You were thankful for that, there were kids around who were a third of your age who’d already done it, they barely even looked legal. You nodded slightly and felt the heat rush to your cheeks.  
“Surely that’s a special gift?” She responded, tossing her wrapper in the trash. You nodded.  
“I think I will” You murmured. Charlie smirked.

“Good girl” She smiled.  
“What else will I need for tonight?” You sighed.  
“Condoms, card, wine maybe?” Charlie suggested, taking a mouthful of her drink.  
“Yeah…” You trailed off, looking at the stores around you.  
“Ooh, nice panties. You’re not wearing those damn granny panties again” Charlie responded. Rolling your eyes, you smirked.  
“You been looking at my panties?” You asked, a raised eyebrow.  
“C’mon, let’s go to VS” Charlie said, quickly changing the topic of conversation. Charlie took your hand and practically dragged you down the street to the store. Walking in, Charlie dragged you to a shelf that had the sexiest pairs of underwear you’d ever seen, though non looked like they’d suit you. Browsing over the various pairs, you settled on a pair that you knew Sam would love. 

 

Returning to the bunker, your arms were laden with bags, and Charlie was following with some candy in her hand.  
“What time is it?” You asked, dumping the bags into yours and Sam’s bedroom.  
“3.30” Charlie said.  
“Alright, I got an hour and half to make myself suitable” You chuckled.  
“Want me to help?” Charlie asked.  
“N-no” You stuttered.  
“I’ll be okay, thank you though. I’ve had fun today” You spoke, quickly making a mask for your insecurities.  
“Alright, but I wanna see you before you go” She said. You nodded and smiled, watching her leave. A sigh left your throat as soon as she left, and you began to set to work. Picking up the dress, you hung it on the closet door and went to shower. Usually, you took a quick five minute shower before a date but with it being a special occasion, you shaved your body. Dean would whine that you hogged the bathroom for so long, but he’d soon top whining. After you had showered and moisturised, you walked into the bedroom and started to dress, making sure you looked your best.

 

4.45 Rolled around and you were just strapping your shoes when Charlie walked in. Her eyes widened when she saw you, clearly not anticipating you to be fully ready.  
“Holy damn” She groaned. You blushed and smiled.  
“Shuddup” You chuckled.  
“No, but seriously, you look genuinely gorgeous” She exclaimed and dragged Dean into the room from the corridor.  
“You sure its Sammy you want (Y/N), cos damn” He groaned. You blushed and rolled your eyes.  
“Where is he?” You asked, biting your lip.  
“Just about ready. He’s in the garage, he’ll be up in a sec but he doesn’t want us here” Dean said.  
“Alright. I’ll see y’all later” You said, when you saw Sam walking down the corridor, hands behind his back.  
“And Charlie, meet me in the library tonight and I’ll tell you all about it” You winked, before moving back into the room. Looking around, you saw the unopened box of condoms and realised that you needed some with you. A knock at the door pulled you from your thoughts. Walking over, you smiled when you found Sam in a suit, once that wasn’t his fed suit.  
“Damn” You murmured, raking your eyes down his body.  
“I think I should be saying that to you” He responded, his eyes resting on the low cut, strapless dress.  
“I will be with you in one moment” You said and moved to the bed, hiding the box of condoms with your body as you put them into the gift bag that had the watch for Sam.  
“I have something for you” He said softly. Once you had knotted the ribbon around the handles of the bag again, you turned to him. He was holding a bouquet of pale pink roses in his hand. You smiled.  
“Why thank you, the other ones you got me were beginning to look a little lonely” You said, nodding towards the white roses. Sam smiled and went to put the roses in the vase with the others.  
“Shall we go?” He asked. You nodded and smiled, following him while checking him out. Walking into the garage, you watched as Sam walked you to the car and opened the passenger side door, allowing you to climb in.  
“Such a gentleman” You smiled and kissed him gently. Sam smiled and rubbed your side, before closing the door and climbing in the driver’s seat.  
“It must be a special event if Dean’s letting you drive” You smiled, watching as Sam began the journey, though where he was going you didn’t know.  
“Yeah, he nearly didn’t. I’m cleaning for the next month” Sam chuckled.  
“Don’t worry, I’m sure I can help and Dean won’t know” You smiled rubbing his thigh. Sam smiled and cupped your hand.  
“I love you, y’know…I know I haven’t been able to show it so much with everything with Dean, but I do love you” He spoke, barley taking his eyes off of the road.  
“I know Sam, it’s been a hard few months for all of us, but we’ve made it through it all...together” You said, kissing his cheek. Sam smiled and the next few minutes of the journey passed in a comfortable silence. Your eyes softened when Sam pulled up at a small clearing, somewhere where there was once a hunt nearby. You’d often walked in the area, knowing just how beautiful the area was. Clearly Sam agreed. He took your hand and helped you out of the car before going to pull a small picnic basket out of the trunk, while you picked up the gift bag with the present you had for him, though no bag would hold the worth of what you were giving to Sam.

“Are you ready?” He asked, holding his arm out for you. You nodded and smiled, taking Sam’s hand. He walked you along the slightly worn stone path. You smiled, your heart swelling when you found a table with a tablecloth and candles. It was framed perfectly by the trees and the moon.  
“I looked at all the restaurants in this area, nothing looked perfect for you. Either too formal, or too casual for the occasion, so I made it myself” He smiled, clearly proud of himself.  
“I love you” You said softly, and kissed him gently. Sam smiled and held your hips.  
“I have to say, you’re looking absolutely gorgeous” He spoke, eyes coming to rest on the low cutting chest. You smirked.  
“Special dress for a special occasion” You smiled, shrugging slightly. Sam smiled and moved to pull a chair back, letting you sit down before moving the table and sitting on the opposite chair.  
“We are having your favourite meal. Turkey and cranberry tortillas, fries and chips, a lil salad and then I have two chocolate muffins for us” He smiled. You smiled widely.  
“Plus, we can always go grab some take-out later if you want it, I know how much you like Chinese” Sam smiled. You smiled and nodded, watching Sam open the basket and pull out the various food items.

 

The night passed with ease, the food being shared. Sam gave you his muffin, claiming he didn’t want to ruin his ‘diet’. As the food basket moved from the table, Sam shifted.  
“Now…I know it’s been a shit year. Between the war in Heaven, everything with the angels and then Dean turning just to make it worse…but there’s only been one consistent in my life…(Y/N)…will you marry me?” Sam asked, shifting to one knee. He pulled the ring box out of his pocket, and the ring was beautiful. It had three beautiful diamonds along the top, it was silver and looked beautiful.  
“Oh my god, Sam yes!” You exclaimed and shifted to hug him tightly, while pulling him close. He smiled widely and kissed you deeply, sliding the ring onto your finger.  
“That makes my present look a bit shit now” You chuckled, pulling the small bag from behind your back. Sam smiled and opened the bag. You saw his eyes fall onto the condom box, but rather than investigating that, he went to the watch box first.  
“(Y/N)…This is beautiful…how did you know I wanted this?” Sam asked, voice full of shock. You blushed and smiled, shrugging slightly.  
“And is this…condoms?” Sam asked, voice filled with confusion as his eyes met yours. You nodded, shifting to look down.  
“(Y/N)…what are you saying?” Sam asked, putting the condoms and watch on the table before cupping your cheeks.  
“I think…I know I’m ready” You murmured. Sam shifted to sit you on the table.  
“Are you sure?” He asked. Nodding, you shifted slightly.  
“Yeah…I’ve never wanted to do it before…it scared me, I never wanted someone to just use me for it…but Sam, you’re different. You wouldn’t do that” You spoke. Sam smiled widely and kissed you deeply, shifting slightly. You moaned.  
“Now?” Sam asked.  
“If you want to” You murmured, shifting when Sam’s head drifted to your neck. His stubble rubbed in just the right way. You would have let Sam take it further, if not for the feel of rain drops hitting your heads.  
“Back to the car?” Sam asked. You nodded in response and watched as Sam picked up the watch and condoms, before running back to the car with you. He opened the back door and you laid on the back seats, while Sam climbed in and closed the door. He kissed you deeply, while your hands dragged over his jacket, until he removed it, along with his shirt, and dropped them on the front seats. You groaned at the sight of his bare chest. It wasn’t the first time you’d seen him topless, in fact it was a common occurrence given he slept topless, but it always made it better when you saw him topless. He groaned and dropped his head to your neck, nipping and biting lightly. You groaned and reached down, unzipping your dress. Sam shifted to sit back, allowing you to remove the dress. You put it onto the front seats, shifting. Now you were left in only the underwear that you’d bought earlier in the day, and the heels. Reaching down, Sam removed your shoes before removing his own.  
“Fuck” You groaned, when Sam reached down to unbutton his trousers and adjust himself in his boxers.  
“I will go slow” He promised. You nodded and shifted, watching as his eyes dropped to your panties.  
“They special for me?” He asked, a small smile. You nodded and grinned.  
“Charlie told me to get them” You smiled. Sam chuckled.  
“You might wanna remove ‘em soon” He chuckled. You nodded and shifted, removing them, tossing them into the front seat.  
“How do you wanna do this?” Sam asked.  
“If you ride me, it’s kinda easier space wise, but I don’t know if it’ll make it easier for you” He said softly.  
“We can do it that way…as long as you go slow” You spoke, shifting. Sam nodded and smiled.  
“Straight into it or…?” Sam asked. You shrugged.  
“I think I just wanna do it…” You spoke, shifting to nip at his neck lightly. Sam smiled and nodded, while reaching for the condoms. You smiled and shifted, watching as Sam moved to push his trousers and boxers to his knees. You groaned.  
“Fuck” You murmured, when you saw just how large he is. Sam chuckled and kissed you, reaching down to finger you lightly. You moaned, head falling to rest on Sam’s shoulder. You moaned and shifted, the feeling of Sam’s fingers inside of you was a foreign experience for you. He smiled and lifted your head with his free hand.  
“This okay?” He asked. You nodded.  
“So good, so okay” You panted, moaning slightly. Sam smiled and nodded.  
“Good” He smiled, spreading his fingers slightly. You moaned and shifted, biting your lip. You could feel a change in your body, something you’d never experienced before. Like a knot tightening, you didn’t know what it was, but you felt the moment it exploded, and Sam knew what it was.  
“Good?” He asked. You groaned and nodded, panting.  
“Amazing…” You murmured.  
“At least I know how to tell when you’ve had an orgasm now” He chuckled.  
“That was an orgasm?” You’ve asked.  
“Yup. Never had one?” He asked. You shrugged and looked down.  
“Well that’s gonna change” Sam promised, kissing you gently, while removing his fingers from you. He reached over and grabbed a condom, rolling it on swiftly.  
“You sure?” He asked, one final time. You nodded and smiled, kissing him gently while shifting for Sam to manoeuvrer you. His hands fell to your hips, guiding you down onto him. He was wide, the head splitting you wider than you could imagine as you slowly dropped down. When Sam was barely halfway inside of you, he paused, allowing you to adjust to his _huge_ size.  
“Fuck” You murmured, resting your head on Sam’s chest.  
“Good?” He asked, shifting one hand to brush his fingers through your hair.  
“Amazing” You murmured, kissing him gently.  
“Just…big” You spoke, shifting slightly.  
“That’s why I stopped, don’t wanna hurt you” Sam said softly. You nodded and smiled, kissing him gently.  
“Go on” You said. Sam nodded and eased you down until you were seated against him. You groaned and shifted.  
“Fuck you’re deep” You murmured. Sam was almost touching your womb. There was no doubt that without a condom, Sam would be able to impregnate you very easily. Groaning at the thought, you slowly rolled your hips, a gasp leaving your throat as you felt Sam move inside of you.  
“Fuck” He murmured, almost silent, yet in the silence of the car it was loud enough.  
“Yeah” You responded, barely able to speak. The pleasure was overwhelming. Sam was hitting deep inside of you, and despite neither of you moving too far, it didn’t take long for you both to be coming, the sound of your groans filling the car.  


You were panting for several moments before Sam shifted, pulling out of you with a hiss.  
“Fuck” You whispered. Sam chuckled and kissed you gently, before pulling the condom off and knotting it.  
“I’m going against all my morals here” He murmured, before tossing the condom out of the car. You smiled and began to redress, with Sam helping you adjust the dress before he pulled his pants and trousers up. He shifted and moved to the front of the car, helping you through. You shifted slightly and wrapped Sam’s jacket around yourself, while you both adjusted yourselves until you looked presentable to Dean.  
“How was it?” Sam asked, putting the car into drive and starting the journey.  
“Amazing…thank you Sam” You smiled. Sam smiled and rubbed your thigh.


End file.
